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Winners & Losers | The Holdout & the Hack

Yes, we know. We didn't have Chuck Schumer on this bingo card, either.

Sam Osterhout's avatar
Sam Osterhout
Mar 30, 2026
∙ Paid

The lack of expertise in the Trump administration — in case it hasn’t dawned on you yet — is a feature, not a bug. Experts annoyingly approach problems with, ahem, expertise. Facts. Data. Experience. Humility.

So if you are the kind of person who believes that tariffs will raise a ton of money from China and make us all rich beyond our wildest dreams, you might want to avoid experts. Or if you feel in your heart of hearts that a war in Iran is a master stroke and will definitely not make you look like an idiot, surround yourself with people like Pete Hegseth and you can go on believin’!

The challenge that experts provide, in most administrations, is a welcome kind of abrasiveness. Surely, nobody likes to be told they’re wrong. Also, clearly, anyone who believes they are deserving of the Presidency is a special kind of narcissist. But it’s that same narcissism that should lead one to rationally want to be proven wrong when one is, in fact, wrong, and when the stakes are global.

An expert can stop you from making a jackass of yourself in front of the entire planet or from blowing up the world.

Trump is different. Watch his Cabinet meetings. The validation he craves is so immediate and immense that he prefers a gushing compliment now than sound advice for later.

I'll Gladly Pay You Tuesday For A Hamburger Today

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The first administration was full (relatively speaking) of people who would say what they needed to say to him and then do the work that needed to get done. They managed to eat the hamburger today AND pay for it on Tuesday. Some of his orders and directives famously just accidentally sat on someone’s desk until he forgot about them. A gushing round of Great ideas! You’re a genius! was often followed by inaction or corrective action.

As destructive as that administration was, it was staffed, generally speaking, by some serious people (*some). Plus, there were whistleblowers, and those who simply refused to be a part of the administration when they realized what was happening.

This time is different. The lesson the true believers learned from Trump 1 was that nobody listened to Trump enough. Trump’s 2’s motto could be Let him cook.

This administration is a sideshow of hucksters, showmen, clowns, and entitled billionaires smelling their own farts. To many of them, Trump has all the expertise anyone needs.

This week’s Loser is a huckster, a showman, and a clown, who aspires to be a fart-sniffing billionaire.

And my Winner is going to elicit a backlash of comments below. I apologize in advance.

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Sean Duffy, Loser

Sean Duffy is a world-champion lumberjack.

I could end this part here. But I’ll go on.

He was a cast member on MTV’s The Real World: Boston, in 1997; Road Rules: All Stars in 1998; and Real World/Road Rules Challenge: Battle of the Seasons in 2002.

He went on to become the co-host of The Bottom Line on Fox Business.

He is now the Transportation Secretary and was the acting administrator of NASA for some reason.

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